I Am Trying to Break Your Heart
by enigmatic darling
Summary: All is bitter in love and war. Four weddings in a span of eight years. Three attempts. Two people. One heartbreak. [Implied Literati]
1. Default Chapter

**Title:** I Am Trying to Break Your Heart

**Disclaimer:** I do not own Gilmore Girls, the characters, or the WB. And if I _did_ would I be here writing fan fiction? ;)

**Dedication:** To **Ari**, **Elise,** **Ilona**, and **Lee** for reading over this and making such wonderful suggestions and pointing things out I would've never noticed. Thank you for being so helpful, specific and supportive.

And to everyone else at the **Lit Thread** at _S-H.org_ just because they're awesome.  I love you guys.

**A/N:** Title comes from the amazing **Wilco**'s _I Am Trying to Break Your Heart._ I highly recommend them, btw. All chapter titles come from the last line of every new verse.

Please R&R.

**Part One:** _What was I thinking when I let go of you_

          The yellow light from the apartment across from him has gone out.

          He blows out a wisp of smoke, holding his own burning cigarette. He follows his old routine, and stubs the cigarette against the concrete, liking the sound of the fire against the cold floor. He takes a minute to look up at the monstrous black sky, hovering over the big city, _daring_ them, before he reaches for another cigarette.

          His fourth.

          That fact does not go unnoticed by him.

          Every night he waits until the small hand hits exactly at the eleven, and the big hand at the nine. At that time, he heads out to his balcony and fits his legs tightly between the concrete and the rusty green railing. By the end of his third cigarette, the lonely old man, directly across from him will turn out his lights. He thinks it might be his future.

          As soon as the fourth cigarette is lit between his fingers, out escapes a bitter, low laugh. He shakes his head once, smokes his cigarette and stares down at the depressing noise of the city. Every night he waits. That was what it was all about, wasn't it? He waits to hear specific sounds, down below. He crosses them off in his head as they are heard. Sometimes, he will deny sleep, staying up until dawn, simply for the sound of a beer bottle being thrown harshly to the ground. As soon as he hears the loud crash, he pictures the broken glass scattered in the street, skidding across, becoming scarred. Then, it is okay to go to sleep.

          Everything must be crossed off his list. He finds that he can't sleep without knowing that his list is marked from top to bottom, nothing left out.

          It is a routine. It has to be completed in a full circle.

          The rest of New York City go through their own routines. Some wake up, kiss their loved ones goodbye, go to work, come home, kiss their loved ones goodnight. Others had simpler routines to follow. They were difficult to break, he had learned. And while others kept their routines for security, his helped him to ignore the growing emptiness in his tired body.

          Like all of them, he went around in a dull circle, never _daring_ to break it. He won't risk it.

          But tonight, under the clear, pitch-black sky, with the slow, thin wind blowing at his side, the chain had broken accidentally. During his _fourth _cigarette. His mind unconsciously wandered off. Drifted back.

          Once routines are broken, you never go back. You start over again. But in his case, with his already destroyed, he went along, going with the flow. From his exterior, he holds the same lifeless character. His back takes its hunch-back form and his legs hang dully above the streets. His cigarette glows between his middle and index fingers. Inside, sparks set off in his head, soon spreading throughout his body.

          And for the first time in three years, he feels alive.

          A blurry picture of a girl begins to form in his mind. He closes his eyes, thinking that maybe it will become clearer. To his surprise, it does. He can see the lines of her face, the curves of her lips, fitted into a small smile. The soft brown hair coming down past her shoulders; her blue eyes sparkle, blinding all that meet them. A sharp pain slides in his chest.

          The image is fading away, morphing into another. Now, she is running in the sand, barefoot, with her hair pinned up, a loose strand hanging from the side of her face, flying as she goes along. Her hands hold the long, white skirt of her dress, saving it from ruin. And she is smiling. Her eyes are gleaming and her smiling matches it well. He can't tell what kind of smile it is; he can't fit it in any category.

          He would like to think it genuine, but the bitter side of him knows the ruthless smile.

          His eyes shoot open, startled by the prick of heat between his fingers. He stubs it against the ground and doesn't find the sound so satisfying all of sudden. He leaves it to burn out as he reaches for a fifth cigarette.

          There has never been a fifth.

          He takes his first taste of a fifth cigarette and discovers that he loves it.

          But it all turns bitter when he blows out the cloud of smoke.

          He thinks of the _fourth_ and her running across the sand, the smile on her face. And then comes the _third_ and the _second_ and then the _first_. The same feeling being repeated over and over again, just building up every time. It all began with the first. It was those first five little words that started every mess he had ever made. Including his routine.

_          "What are you doing here?"_


	2. Sookie and Jackson

_I Am Trying to Break Your Heart_

****

**Disclaimer: **I do not own Gilmore Girls, the characters, or the WB. And if I _did_ would I be here writing fan fiction? ;)

Dedicated to Lee, Elise, and Ari. Thanks to all three of you for being so helpful and letting me attack you with this fic. :) You're the best. Read their fics… or else. ;)

****

**Part Two: **_What was I thinking when I said it didn't hurt_

**Summer of 2002.**

_You are cordially invited to…___

_Sookie St. James and Jackson Melville's_

_Wedding_

The sun is situated high in the perfect summer sky. Streaks of white accompany the pale blue, resembling delicate lace. Stars Hollow buzzes with its normal excitement; talk of a wedding seems to be the main topic of conversation.

Luke's Diner overcrowds with people; it is the time of day where Luke becomes too busy to notice much of anything. Whether it is a cell phone ringing, Taylor Doose, or his seventeen-year-old nephew sneaking up the stairs.

He tosses his bag near his bed, and hears the thump of the weight against the carpet as he walks towards the window. He holds the thin fabric of the curtains between his fingers. The light shines through, blinding him for a second before a picture comes into view; a fairytale town: Hell. Thoughts of a private school girl paying him a surprise visit enter his mind.

He turns away from the window, and lets go of the curtain.

The room is dark again.

He sighs and feels his shoulders falter.

-

The words meld in with each other, making it impossible to read. He has always felt when another person's presence was near for as long as he can remember. Sometimes, it began as a prick at his neck; gradually, it made a route throughout his body; heat in his skin. But most of the time, it was simply a dull feeling that filled his mind.

He stares down at the book, waiting to hear the crash of the door against its frame. He hears it: the door, the shuffle of feet, and then a sharp intake of breath.

He looks up; knowing who it is and then he sets aside the book on his shelf. They stand in silence for a while before an official greeting. "Hey."

"Hey," he replies. Nonchalant. His signature.

"How'd you get in here?" he asks, gesturing around the apartment.

"The door was open." A smart-ass reply. He looks at the door for a split-second before he returns his attention to Luke.

"No, I mean, I was in the diner. I would have seen you come up the stairs… you know what, forget it, I don't wanna know," he says, waving it off. "So, how's everything back home?"

"Fine."

"Your mom?"

"Fine."

He tries to get to what he thinks is the point, "You in trouble?"

"Nah." _Depends what kind_, he thinks.

"Then what the hell you doing here, Jess?" He looks for some kind of answer, but as usual, receives nothing but a bored stare.

"You know, I, uh, I called you six times. Now I didn't expect you to call me back so we could sit on the phone in bed and watch _Sleepless in Seattle_ together. I just expected you to call me back, say you got home, say no one mugged me on the bus, say you were okay. Say…" His words trail off, leaving it up to Jess to wonder what else there was to say. He didn't know.

"You know what, never mind. Just tell me what it is you want. I got work to do."

He looks to the floor, instantly remembering the smile that had stolen her lips when she had found him. Hope had sparked then. It was a burning feeling that he carried with him these days. "I wanna come back."

"You what?" he asks, not believing his ears. It didn't help that Jess mumbled.

Jess looks at him in the eye. "I want to come back."

"Come back here?"

"Yes."

"Here to Stars Hollow?"

"Yes."

"To live in this apartment with me?"

Tired, he replies, "I said yes a million times already."

"You know what, you're the one asking for something so you don't get to be James Dean this time, okay? Now, one more time, you wanna come back?"

There is a surprised, disbelieving tone in his question. And Jess can't blame him. He had always shown Luke the attitude that he wanted to get out of here. He had said it to Rory herself, _"I plan to get out of Stars Hollow." _He still does_--_doesn't plan to live here the rest of his life. But she had done something to him--convinced him. Rory had showed him that this town—a town that he despised, didn't have to be so bad. It could be worth it.

"Yes."

"Why?"

If he had answered that question truthfully, he could have been walking over Luke's body shaking with laughter seconds later. "I just, I… I just want to come back."

The next thing he knows, Luke's on a rant. He half-listens, half believes that his bag would never be unpacked. He picks up on certain things: Jodie Foster. Letters. Crazy. Chaos and havoc you've wreaked. Butt with hands. And the tired words: You wanna come back?

He walks around Luke and points to his books. "You didn't pack up my stuff yet," trying to make some nonsense point.

"Uh, no, I've been a little busy," he replies.

"When were you planning on sending it back to me?"

"What, hey, am I wearing a little brown uniform with UPS stamped on it?" Smart-ass reply. The scoreboard is tied now.

He nods, simply, getting a taste of his own medicine. "So, what do you think?" There's a strange thickness of desperation in his voice that he doesn't realize is there, yet Luke catches it, and is surprised to hear it.

"Things are gonna have to be different, Jess."

"I know."

A moment of hesitation, and then, "Okay."

"Okay?" His voice sounds like it came from the mouth of a little boy on Christmas morning. Surprised. Hopeful.

"So you're staying."

"I'm staying." His lips curl up a little.

"Okay, then. Stay. I gotta get back to the diner." He makes a move to leave.

"I'll help you close up late, all right?"

"Sure." Luke thinks things will be different. He believes Jess will be different. He thinks he is going to try.

Jess nods simply and walks towards the exit, planning to pay Rory his own surprise visit. Or, more correctly, return. He scratches his head, thinking of what to say when Luke's voice stops him.

"She's not home."

"Who?" he asks, stupidly.

"She's at Sookie's wedding, with Dean, they're still together. They seem to have gotten through the whole car incident. They're doing really good, Dean and Rory," he explains.

"Good," he responds, disbelieving, not ready to let go of the spark.

"Just leave it alone, Jess. She's got a boyfriend. Just let it go…"

He tries to ignore the fact that Luke had seen through him. He turns to look at Luke, "I don't know what you're talking about. I'm just going out for a walk." He turns around and makes his way to the door.

"You heard what I said?"

"Yeah, I heard what you said."

He slams the door shut.

Luke sighs, his earlier thoughts erased.

-

He walks out of the diner, cool air and warm sun meeting him. He squints away from the sun and stuffs his hands in his pockets, unsure. He begins to walk towards the bridge, hoping something would come up. He walks through the town square, thinking of Rory. He hadn't really thought of what he had been doing when he caught that bus back to Hartford. He had felt _something--knew _something, and he followed that sensation back.

He looks up and sees two women chatting nearby; he doesn't pay much attention until he hears the name 'Sookie'. He slows his pace, trying to keep it cool while trying to catch some information.

"You heading to the wedding?" the first woman asks.

"Oh, no, wasn't invited."

"That's a shame; I'm heading over there now. The Independence Inn is so _lovely _during this time of year."

"_Beautiful _place for a wedding. Why, just a few months ago…"

He smirks, thanking the old women silently. He turns and heads in another direction.

-

He looks up at the Independence Inn and finds a way to enter without going through the entrance. He notices how large the area is and notices all the guests by the back porch, talking and laughing, wine glasses in their hands. He heads out the same way he came in and continues up the dirt road he had come down on. He hopes to find a way to get to the back, and is successful.

He glances around his surroundings and spots the lake about one hundred feet away. He looks at where he stands and wonders how in the world he is going to find her. He might has well have been standing in an airport.

It's just his luck that he finds her walking with her dad a few yards away. He watches them for a while, keeping his arms behind him, remembering the one time her father had been in town. Jess had seen him around, back in October when Rory had her cotillion. He still remembers the white dress with its long full skirt that she had worn. She looked like the pinnacle of a wedding cake.

They embrace, and then he walks off, cell phone in hand. She stands alone for a second, before she slowly turns around and meets his eyes. A questionable expression is all that she gives him as she walks towards him. He takes small steps, meeting her halfway.

There is a slight change in the air that he breathes--thinner, if possible.

"What are you doing here?" It's the first thing she says to him; she greets him with more emotion. Wonder. Surprise. Nervousness.

"Hello to you too," he replies.

"Is everything okay?"

He looks down at her blue dress that matches her eyes, and her hair that reminds him of child innocence. "You look nice," he says, afraid he'll answer her question truthfully.

"Thank you," she responds, as she fiddles with her hands a little. "What are you doing here?"

He wastes no time, wanting her to know that he has come back. He wants her to know that she is to blame, that she has caused him to make this move, but he will never be able to put it into words. "I moved back."

"What?" She is shocked to hear it. But there's no hint at whether she is unhappy at his words.

"I moved back," he repeats.

There is a prick of heat at the bottom of his neck. It spreads through out his body, filling it with warmth. There is no new presence, just a single realization, slowly dawning on them both.

"But—what—why?" she struggles to get the words out.

"Just… wanted to." She looks into his eyes and meets what has been there for the past seven months: Desire. There's a shine of hope and a hint of fear, as well. She stands still for a second, and for a moment, he thinks that she finally understands.

She moves quickly; closes the gap between them and takes hold of him, capturing his lips. It takes him a split-second for him to respond, for him to process the information. He draws her in closer, placing his hand on her cheek, simply thinking about how perfectly her lips fit against his.

He begins to feel her slip away, and his hands drop to her sides. The burning warmth that had once filled his body blows out slowly. A pain begins at his neck and starts to move downward. She realizes her actions, now, looking pained. His eyes plead with her not to run or turn away, but she does anyway.

"Rory—" he begins, ready to dismiss the kiss for her: a lie at his throat.

She turns around with an expression he cannot place. "Don't say a word!"

"Okay," he says simply. He will obey her request.

"I have to go," she says.

He watches as she runs off, not knowing what to make out of it. And then, she turns around, yelling out to him, "Welcome home!"

The corners of his lips move slightly upward as they part open, and then close again, pressing into a thin line. He looks to where she once stood and looks away, the pain subsiding. An all too-familiar feeling takes its place.

He allows his shoulders to fall, the weight becoming too much to carry.

He sighs.

She was gone.

-

He waited for weeks.

He would stop in his tracks at the sound of her name, only to find out that it was simply a reminder that she wasn't there. He knew. The constant tugs at his heart, the whispers of _false hope_ in his mind, and the dim blonde he calls his girlfriend reminded him of that fact.She was gone.  
  
It still hadn't stopped him from thinking about her. Nothing stopped the penetrating feeling when he repeated the kiss in his head.  
  
In the back of his mind, he thought she would call. He thought he might find a message on his answering machine, greeting him with an unsure voice; maybe a letter with the return address being _Washington D.C._There are no letters. There are no calls. There is just a crack in his heart that he pretends isn't there.  
  
-  
  
He enters the apartment with his jacket in his hand, coming home after a night with Shane. The irritating melody of the Summer Festival continues to be played, it fills the apartment, along with the thick summer air.  
  
"Hey. You just get home?" Luke asks, coming out of the bathroom.  
  
"Yup."  
  
He tosses his jacket across his bed and crashes upon it, taking a book along with him. He begins to half-read, and half-listen to the movement of feet on the floor, coming towards him.  
  
Luke stands at the foot of his bed with his hands in his pockets, watching him as he reads. "Gonna head to sleep soon?"  
  
"Yeah."  
  
He nods but doesn't make a move.  
  
"Something else?" he asks, as he turns the page.  
  
"She's home, you know."  
  
A mixture of bitterness and anticipation fill his body as he hears the words. Calmly, he asks: "Who?"  
  
"You know who," he responds, a little annoyed at his mask of stupidity.  
  
He only nods in return.  
  
-  
  
She avoids the diner for a few days.  
  
Frankly, he is sick of it. He's tired looking up to the sound of the bell, only to find a middle-aged woman or an old couple. He is fed up with being let down again and again. He finally decides he isn't going to wait around for her anymore; isn't going to wait for her to show up and confront him.  
  
He can't take it anymore.  
  
He goes out to look for her.  
  
-  
  
He finds her in the first place he looks: Doose's. He walks in and sees her by the tater tots, and casually walks towards the canned-food aisle. He picks up a can of beans, and pretends to be interested in the item. In a matter of seconds, a prick at his neck begins.  
  
When he looks up, she's standing there with a basket in her hands, almost afraid. She hides it well. It takes him a moment to gather himself (to remember words). She's really there.  
  
"Doing a little shopping?"  
  
"Yes," she responds, walking forward, attempting an escape.  
  
He isn't letting her get away this time. He sets the can back down on the shelf, blocking her exit.  
  
"Excuse me," she says a hint of annoyance.  
  
"Why the cold shoulder?" he's slightly irritated as well.  
  
"No cold shoulder. I just have perishables here."  
  
"Oh yeah, you wanna get home before that beefaroni goes bad," he replies, taking a peek at her basket.  
  
"My mom's waiting for me," she responds, walking past him. He follows her to the check out line.  
  
"How was Washington?"  
  
_How much fun did you have while ignoring me?_  
  
"Fine."  
  
"Do anything interesting?"  
  
"Nope."  
  
"Okay." He looks down to the floor, unsure of what to say next. He needs to talk to her about this but can't find a place to begin.  
  
"What about you?"  
  
"What about me?"  
  
_Did you suddenly remember me?_  
  
"Anything interesting happen? This summer, I mean."  
  
"Nope."  
  
"Really?" she asks, not believing him at all.  
  
"Really."  
  
"So nothing happened this summer, at all?" she asks, her tone somewhat accusing   
  
"It was hot. Two weeks ago there was a run on snow cones. Machine broke, people went crazy, Taylor tried to call in the National Guard, but –" Halfway through his sentence, she walks towards the check out line. He follows.  
  
She places her basket down. "I'm not talking about snow cones," she interrupts, frustrated that he won't tell her the truth. Or anything.  
  
"What are you talking about then?"  
  
He has an idea of what she's trying to get at.  
  
He wants to hear it from her.  
  
"Nothing," she says with a sigh.  
  
A pause. Uncomfortable silence. The air was warm for a store; the lights beat down on his back. Beads of sweat begin to form.  
  
He gives in (like he always has), not able to take it any longer. "Her name's Shane."  
  
"As in 'come back'?"  
  
"Yup."  
  
"Well, great. That's great." She looks at his doubtful face, "Really, it's great."  
  
"So I've heard."  
  
"Well it is."  
  
"Are you upset about something?"  
  
"No."  
  
He tries to step forward, try to clear things up. "I mean, me and Shane--"  
  
"What about you and Shane?"  
  
"I don't know, it didn't exactly bring a smile to your face."  
  
"Well, I'm still freaked out about the, uh, snow cone machine."  
  
"Okay," he responds, uncertain.  
  
"I could care less about you and Shane."  
  
"Good." He's sick of this conversation; a conversation that isn't going much anywhere.  
  
"It just surprised me, that's all."  
  
His raises his eyebrows, "Why?"  
  
"Because."  
  
"Going to need a clearer answer then that, Rory."  
  
"Because of what happened at Sookie's wedding."  
  
"Ah."  
  
He thinks about it again, the kiss. Something pulls at his heart tiredly.  
  
"Yeah, so me coming back here and just seeing you with Shane just kind of threw me for a sec."  
  
It's the final blow.  
  
The pain explodes--everywhere. In his head… in his chest… in his entire body. Sparks are shooting off his arms. "I'm sorry, did I hear from you all this summer?" She opens her mouth to speak, but there is nothing for her to say. She couldn't defend herself on this one.  
  
"Did I just happen to miss the thousands of phone calls you made to me, or did the postman happen to lose all those letters you wrote to me? You kiss me, you tell me not to say anything…very flattering, by the way. You go off to Washington… then nothing. Then you come back here all put out because I didn't just sit around and wait for you like Dean would've done?" Her eyes widen, something ringing true—something that she wants to hide.  
  
"And yeah, what about Dean? Are you still with him? 'Cause last time I checked, you were, and I haven't heard anything to the contrary. Plus, the two of you walking around the other day like some damn Andy Hardy movie. Seemed to me like you're still pretty together. I half expected you to break into a barn and put on a show."  
  
"When did you see me with Dean?" she asks.  
  
"At that stupid summer insanity plea the town put on."  
  
"Oh, I'm surprised you could see anything with Shane's head plastered to your face," she retorts.  
  
"You didn't answer me."  
  
"About what?"  
  
"Did you call me at all?"  
  
"No."  
  
"Did you send me a letter?"  
  
"No."  
  
"Postcard?"

"No."  
  
"Smoke signal?"  
  
"Stop."  
  
"A nice fruit basket?"  
  
"Enough!"  
  
"Are you still with Dean?" She remains silent for a moment, torn between telling the truth or a lie. "Come on, Rory, yes or no--are you still with Dean?"  
  
"Yes, I'm still with Dean," she answers.  
  
He nods and shakes his head at the floor. He laughs bitterly and looks up, searching her eyes. "What is wrong with you?"  
  
"Excuse me?"  
  
He ignores her question and backs away. "String Dean along all you want, but I'm not going to be a part of your game."  
  
He turns around and is ready for the weeks of torture to come. But, then, he stops at the sound of her voice. "Did it hurt?"  
  
"Excuse me?" he asks, turning around to face her.  
  
"Did it hurt when I didn't contact you this summer?"  
  
He doesn't respond, but she thinks his silence means yes.  
  
"You got over it pretty quickly."

He does nothing to contradict her last statement but shake his head. She'll never believe him. "How about you? Does it hurt when you see me and Shane?"  
  
"No." And by the way she was looking at him, he knew she was lying. But he won't press. "Does it hurt when you see me and Dean?"  
  
"No," he answers simply.  
  
She searches his eyes, but they are nothing but a solid dark brown.  
  
"See you around," he says simply.  
  
And with that, he is gone.  
  
-  
  
It killed him to say no to her question in the market. But he had only done it for her. It would become a pattern for years to come; he will never say what he wants or needs to say. For her.  
  
It always comes down to her.

**A/N: **Confusing? Really? Don't make me dance! :P It comes together in the end.

… An evil plot to keep you readers reading? Maybe. ;)

Oh, and please review. I like them very much. :)


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